TWI355382B - A method of manufacturing ethylene oxide - Google Patents

A method of manufacturing ethylene oxide Download PDF

Info

Publication number: TWI355382B
Authority: TW; Taiwan
Prior art keywords: epoxidation; catalyst; amount; carbon dioxide; feed
Prior art date: 2003-02-28

Application number

TW093104931A

Other languages

English (en)

Chinese (zh)

Other versions

TW200427675A (en

Inventor

Wayne Errol Evans

Marek Matusz

Raa Arend Jan Te

Original Assignee

Shell Int Research

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2003-02-28

Filing date

2004-02-26

Publication date

2012-01-01

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=32962537&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=TWI355382(B) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

2004-02-26 Application filed by Shell Int Research filed Critical Shell Int Research

2004-12-16 Publication of TW200427675A publication Critical patent/TW200427675A/zh

2012-01-01 Application granted granted Critical

2012-01-01 Publication of TWI355382B publication Critical patent/TWI355382B/zh

Links

IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 title claims abstract description 23
238000004519 manufacturing process Methods 0.000 title claims abstract description 13
239000003054 catalyst Substances 0.000 claims abstract description 121
238000006735 epoxidation reaction Methods 0.000 claims abstract description 82
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims abstract description 66
229910002092 carbon dioxide Inorganic materials 0.000 claims abstract description 34
239000001569 carbon dioxide Substances 0.000 claims abstract description 33
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 20
239000001301 oxygen Substances 0.000 claims abstract description 20
229910052760 oxygen Inorganic materials 0.000 claims abstract description 20
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims abstract description 18
239000005977 Ethylene Substances 0.000 claims abstract description 18
238000000034 method Methods 0.000 claims description 30
238000006243 chemical reaction Methods 0.000 claims description 18
229910052709 silver Inorganic materials 0.000 claims description 17
239000004332 silver Substances 0.000 claims description 17
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 17
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 14
239000000463 material Substances 0.000 claims description 11
238000007254 oxidation reaction Methods 0.000 claims description 10
230000001737 promoting effect Effects 0.000 claims description 9
239000007809 chemical reaction catalyst Substances 0.000 claims description 4
PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 claims description 3
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 3
229910052703 rhodium Inorganic materials 0.000 claims description 2
239000010948 rhodium Substances 0.000 claims description 2
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 2
238000007363 ring formation reaction Methods 0.000 claims description 2
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims 4
229910052797 bismuth Inorganic materials 0.000 claims 2
JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 claims 2
238000002309 gasification Methods 0.000 claims 1
230000000694 effects Effects 0.000 abstract description 22
230000003197 catalytic effect Effects 0.000 abstract description 7
BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 15
239000007789 gas Substances 0.000 description 12
239000000203 mixture Substances 0.000 description 10
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 9
229910052751 metal Inorganic materials 0.000 description 8
239000002184 metal Substances 0.000 description 8
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
229910052783 alkali metal Inorganic materials 0.000 description 6
150000001340 alkali metals Chemical class 0.000 description 6
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 5
KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 5
230000007423 decrease Effects 0.000 description 5
229910052707 ruthenium Inorganic materials 0.000 description 5
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
125000004432 carbon atom Chemical group C* 0.000 description 4
150000001875 compounds Chemical class 0.000 description 4
239000002826 coolant Substances 0.000 description 4
230000003647 oxidation Effects 0.000 description 4
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
230000000052 comparative effect Effects 0.000 description 3
-1 floating Substances 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
239000004593 Epoxy Substances 0.000 description 2
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
229910021529 ammonia Inorganic materials 0.000 description 2
239000002585 base Substances 0.000 description 2
230000001186 cumulative effect Effects 0.000 description 2
150000002739 metals Chemical class 0.000 description 2
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
230000001590 oxidative effect Effects 0.000 description 2
238000012545 processing Methods 0.000 description 2
229910001220 stainless steel Inorganic materials 0.000 description 2
239000010935 stainless steel Substances 0.000 description 2
229910052717 sulfur Inorganic materials 0.000 description 2
239000011593 sulfur Substances 0.000 description 2
238000010998 test method Methods 0.000 description 2
238000012360 testing method Methods 0.000 description 2
238000004438 BET method Methods 0.000 description 1
235000017166 Bambusa arundinacea Nutrition 0.000 description 1
235000017491 Bambusa tulda Nutrition 0.000 description 1
244000025254 Cannabis sativa Species 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
229910052684 Cerium Inorganic materials 0.000 description 1
VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
241000196324 Embryophyta Species 0.000 description 1
OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 1
ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
244000061176 Nicotiana tabacum Species 0.000 description 1
235000002637 Nicotiana tabacum Nutrition 0.000 description 1
244000082204 Phyllostachys viridis Species 0.000 description 1
235000015334 Phyllostachys viridis Nutrition 0.000 description 1
239000005864 Sulphur Substances 0.000 description 1
244000269722 Thea sinensis Species 0.000 description 1
229910021536 Zeolite Inorganic materials 0.000 description 1
239000006096 absorbing agent Substances 0.000 description 1
239000002253 acid Substances 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
229910052787 antimony Inorganic materials 0.000 description 1
WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 1
239000011425 bamboo Substances 0.000 description 1
235000013361 beverage Nutrition 0.000 description 1
150000001721 carbon Chemical class 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
GWXLDORMOJMVQZ-UHFFFAOYSA-N cerium Chemical compound [Ce] GWXLDORMOJMVQZ-UHFFFAOYSA-N 0.000 description 1
HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 1
229910052804 chromium Inorganic materials 0.000 description 1
239000011651 chromium Substances 0.000 description 1
239000004927 clay Substances 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
239000002537 cosmetic Substances 0.000 description 1
230000007812 deficiency Effects 0.000 description 1
238000010586 diagram Methods 0.000 description 1
HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
DKQVJMREABFYNT-UHFFFAOYSA-N ethene Chemical group C=C.C=C DKQVJMREABFYNT-UHFFFAOYSA-N 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
229960003750 ethyl chloride Drugs 0.000 description 1
235000013305 food Nutrition 0.000 description 1
238000009472 formulation Methods 0.000 description 1
238000010574 gas phase reaction Methods 0.000 description 1
239000001307 helium Substances 0.000 description 1
229910052734 helium Inorganic materials 0.000 description 1
SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
JMBPWMGVERNEJY-UHFFFAOYSA-N helium;hydrate Chemical compound [He].O JMBPWMGVERNEJY-UHFFFAOYSA-N 0.000 description 1
239000007791 liquid phase Substances 0.000 description 1
VUZPPFZMUPKLLV-UHFFFAOYSA-N methane;hydrate Chemical compound C.O VUZPPFZMUPKLLV-UHFFFAOYSA-N 0.000 description 1
239000003607 modifier Substances 0.000 description 1
229910052750 molybdenum Inorganic materials 0.000 description 1
239000011733 molybdenum Substances 0.000 description 1
239000003345 natural gas Substances 0.000 description 1
150000002894 organic compounds Chemical class 0.000 description 1
150000002923 oximes Chemical class 0.000 description 1
150000002924 oxiranes Chemical class 0.000 description 1
239000002245 particle Substances 0.000 description 1
150000003138 primary alcohols Chemical class 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000004575 stone Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
150000003535 tetraterpenes Chemical class 0.000 description 1
235000009657 tetraterpenes Nutrition 0.000 description 1
229920001169 thermoplastic Polymers 0.000 description 1
238000012546 transfer Methods 0.000 description 1
WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
229910052721 tungsten Inorganic materials 0.000 description 1
239000010937 tungsten Substances 0.000 description 1
239000002023 wood Substances 0.000 description 1
239000010457 zeolite Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D301/00—Preparation of oxiranes
- C07D301/02—Synthesis of the oxirane ring
- C07D301/03—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds
- C07D301/04—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds with air or molecular oxygen
- C07D301/08—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds with air or molecular oxygen in the gaseous phase
- C07D301/10—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds with air or molecular oxygen in the gaseous phase with catalysts containing silver or gold
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Epoxy Compounds (AREA)
Catalysts (AREA)

TW093104931A 2003-02-28 2004-02-26 A method of manufacturing ethylene oxide TWI355382B (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US45084803P	2003-02-28	2003-02-28

Publications (2)

Publication Number	Publication Date
TW200427675A TW200427675A (en)	2004-12-16
TWI355382B true TWI355382B (en)	2012-01-01

Family

ID=32962537

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
TW093104931A TWI355382B (en)	2003-02-28	2004-02-26	A method of manufacturing ethylene oxide

Country Status (13)

Country	Link
EP (1)	EP1611117B1 (de)
JP (2)	JP5373266B2 (de)
KR (1)	KR101107426B1 (de)
CN (1)	CN100400524C (de)
AT (1)	ATE524453T1 (de)
BR (1)	BRPI0407852A (de)
CA (1)	CA2517360C (de)
ES (1)	ES2373037T3 (de)
MX (1)	MXPA05009012A (de)
MY (1)	MY153179A (de)
RU (1)	RU2378264C2 (de)
TW (1)	TWI355382B (de)
WO (1)	WO2004078737A1 (de)

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* Cited by examiner, † Cited by third party
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US7977274B2 (en)	2006-09-29	2011-07-12	Sd Lizenzverwertungsgesellschaft Mbh & Co. Kg	Catalyst with bimodal pore size distribution and the use thereof
TWI446964B (zh)	2007-05-09	2014-08-01	Shell Int Research	環氧化催化劑，製備該催化劑之方法及製備烯烴氧化物、１，２-二醇、１，２-二醇醚、１，２-碳酸酯或烷醇胺之方法
TWI464154B (zh) *	2007-05-09	2014-12-11	Shell Int Research	製備烯烴氧化物、１，２－二醇、１，２－二醇醚、１，２－碳酸酯或烷醇胺之方法
US7553980B2 (en) *	2007-09-26	2009-06-30	Sd Lizenzverwertungsgesellschaft Mbh & Co. Kg	Process for initiating a highly selective ethylene oxide catalyst
JP5194727B2 (ja) *	2007-11-12	2013-05-08	三菱化学株式会社	オレフィンオキシドの連続製造方法
WO2009088040A1 (ja) *	2008-01-11	2009-07-16	Nippon Shokubai Co., Ltd.	エチレンオキシド製造用触媒およびエチレンオキシドの製造方法
JP5868703B2 (ja) *	2008-05-07	2016-02-24	シエル・インターナシヨナル・リサーチ・マートスハツペイ・ベー・ヴエー	オレフィンオキシド、１，２−ジオール、１，２−ジオールエーテル、１，２−カーボネートまたはアルカノールアミンの製造方法
CN102056909B (zh)	2008-05-07	2014-03-05	国际壳牌研究有限公司	环氧化工艺的开车方法及环氧乙烷、1，2-二醇、1，2-二醇醚、1，2-碳酸酯或链烷醇胺的制备方法
US20110152073A1 (en)	2009-12-23	2011-06-23	Scientific Design Company, Inc.	Epoxidation process and microstructure
RU2581365C2 (ru)	2010-09-29	2016-04-20	Шелл Интернэшнл Рисерч Маатсхаппий Б.В.	Способ получения этиленоксида с улучшенным регулированием
US8742147B2 (en)	2010-12-08	2014-06-03	Shell Oil Company	Process for improving the selectivity of an EO catalyst
US8742146B2 (en)	2010-12-08	2014-06-03	Shell Oil Company	Process for improving the selectivity of an EO catalyst
EP2714670B2 (de)	2011-04-29	2022-03-02	Shell Internationale Research Maatschappij B.V.	Verfahren zur verbesserung der selektivität eines eo-katalysator
KR102203848B1 (ko)	2013-03-15	2021-01-15	다우 테크놀로지 인베스트먼츠 엘엘씨.	에틸렌 옥사이드의 제조 방법
CN105228990B (zh) *	2013-04-15	2018-01-30	科学设计有限公司	环氧化工艺
CN106311232A (zh) *	2015-07-02	2017-01-11	中国石油化工股份有限公司	银催化剂、用其制备环氧乙烷的方法及制备乙二醇的方法
EP3548471B1 (de)	2016-12-02	2021-05-19	Shell Internationale Research Maatschappij B.V.	Verfahren zur konditionierung eines ethylenepoxidationskatalysators und zugehörige verfahren zur herstellung von ethylenoxid
US10941093B2 (en)	2017-06-23	2021-03-09	Haldor Topsøe A/S	Process for oxidation of a lower alkane at low temperatures in ammonia-containing gas mixtures
CA3065667A1 (en)	2017-06-23	2018-12-27	Haldor Topsoe A/S	A process for oxidation of a lower alkene at low temperatures in ammonia-containing gas mixtures
CN110357837B (zh) *	2018-03-26	2021-07-02	中国石油化工股份有限公司	一种乙烯环氧化方法

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CA128689A (en) *	1910-05-16	1910-10-18	Thomas Griffith Donaldson	Car door lock
JPS6110570A (ja) *	1984-06-25	1986-01-18	Mitsui Toatsu Chem Inc	エチレンオキシドの製造方法
CN1010585B (zh) *	1984-09-12	1990-11-28	帝国化学工业公司	环氧乙烷的生产
GB8423044D0 (en) *	1984-09-12	1984-10-17	Ici Plc	Production of ethylene oxide
CN1031044C (zh) *	1989-04-18	1996-02-21	联合碳化化学品及塑料有限公司	增强活性和/或稳定性的烯化氧催化剂
CA1337722C (en) *	1989-04-18	1995-12-12	Madan Mohan Bhasin	Alkylene oxide catalysts having enhanced activity and/or stability
GB9107345D0 (en) *	1991-04-08	1991-05-22	Ici Plc	Production of ethylene oxide
US5112795A (en) *	1990-10-12	1992-05-12	Union Carbide Chemicals & Plastics Technology Corporation	Supported silver catalyst, and processes for making and using same
JP2000044331A (ja)	1998-05-22	2000-02-15	Sumitomo Chem Co Ltd	α―アルミナ触媒担体、その製造方法、該触媒担体を用いた触媒
US6372925B1 (en) *	2000-06-09	2002-04-16	Shell Oil Company	Process for operating the epoxidation of ethylene
JP3923289B2 (ja) *	2000-08-24	2007-05-30	株式会社日本触媒	酸化エチレン製造用触媒の担体、その担体を用いた酸化エチレンの製造用触媒及び酸化エチレンの製造方法

2004
- 2004-02-25 MY MYPI20040624A patent/MY153179A/en unknown
- 2004-02-26 EP EP04715069A patent/EP1611117B1/de not_active Revoked
- 2004-02-26 BR BRPI0407852-7A patent/BRPI0407852A/pt not_active Application Discontinuation
- 2004-02-26 ES ES04715069T patent/ES2373037T3/es not_active Expired - Lifetime
- 2004-02-26 CA CA2517360A patent/CA2517360C/en not_active Expired - Fee Related
- 2004-02-26 KR KR1020057015954A patent/KR101107426B1/ko not_active Ceased
- 2004-02-26 CN CNB2004800053910A patent/CN100400524C/zh not_active Ceased
- 2004-02-26 TW TW093104931A patent/TWI355382B/zh not_active IP Right Cessation
- 2004-02-26 WO PCT/US2004/005774 patent/WO2004078737A1/en not_active Ceased
- 2004-02-26 RU RU2005130175/04A patent/RU2378264C2/ru not_active IP Right Cessation
- 2004-02-26 AT AT04715069T patent/ATE524453T1/de not_active IP Right Cessation
- 2004-02-26 MX MXPA05009012A patent/MXPA05009012A/es active IP Right Grant
- 2004-02-26 JP JP2006508853A patent/JP5373266B2/ja not_active Expired - Fee Related
2013
- 2013-06-06 JP JP2013119467A patent/JP2013237671A/ja active Pending

Also Published As

Publication number	Publication date
ES2373037T3 (es)	2012-01-30
TW200427675A (en)	2004-12-16
JP5373266B2 (ja)	2013-12-18
KR101107426B1 (ko)	2012-01-18
EP1611117A1 (de)	2006-01-04
CA2517360C (en)	2012-09-11
ATE524453T1 (de)	2011-09-15
RU2005130175A (ru)	2006-03-27
JP2006521380A (ja)	2006-09-21
MY153179A (en)	2015-01-29
RU2378264C2 (ru)	2010-01-10
MXPA05009012A (es)	2005-10-18
CA2517360A1 (en)	2004-09-16
CN100400524C (zh)	2008-07-09
EP1611117B1 (de)	2011-09-14
KR20050113619A (ko)	2005-12-02
BRPI0407852A (pt)	2006-03-01
JP2013237671A (ja)	2013-11-28
CN1802363A (zh)	2006-07-12
WO2004078737A1 (en)	2004-09-16

Legal Events

Date	Code	Title	Description
2015-11-06	MC4A	Revocation of granted patent

Publication	Publication Date	Title
TWI355382B (en)	2012-01-01	A method of manufacturing ethylene oxide
TWI374773B (en)	2012-10-21	Process for the production of an olefin oxide
TWI283242B (en)	2007-07-01	A method for the start-up of an epoxidation process and a process for the epoxidation of an olefin
CA2490892C (en)	2012-03-20	A method for the start-up of an epoxidation process, a catalyst and a process for the epoxidation of an olefin
TWI333951B (en)	2010-12-01	Method of improving the operation of a manufacturing process
KR101324286B1 (ko)	2013-11-01	저농도 산화 성분의 존재하의 불활성 기체 중에서의 하소
JP5889528B2 (ja)	2016-03-22	エポキシ化触媒、触媒を調製するための方法および酸化オレフィン、１，２−ジオール、１，２−ジオールエーテル、１，２−カーボネートまたはアルカノールアミンを製造する方法。
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